4-(3-Amino-imidazo[1,2-a]pyrazin-2-yl)-benzoic acid methyl ester | 268737-27-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(3-Amino-imidazo[1,2-a]pyrazin-2-yl)-benzoic acid methyl ester
• 英文别名: Methyl 4-(3-aminoimidazo[1,2-a]pyrazin-2-yl)benzoate；methyl 4-(3-aminoimidazo[1,2-a]pyrazin-2-yl)benzoate
• CAS: 268737-27-5
• 化学式: C₁₄H₁₂N₄O₂
• 分子量: 268.275
• InChiKey: VUGVUSHHLLIKBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  82.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-甲氧基苯甲醛 、 4-(3-Amino-imidazo[1,2-a]pyrazin-2-yl)-benzoic acid methyl ester 在 sodium cyanoborohydride 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以24%的产率得到4-[3-(4-Methoxy-benzylamino)-5,6,7,8-tetrahydro-imidazo[1,2-a]pyrazin-2-yl]-benzoic acid methyl ester
  参考文献：
  名称：

  A novel dealkylation affording 3-aminoimidazo[1,2-a]pyridines: access to new substitution patterns by solid-phase synthesis

  摘要：

  The three-component synthesis of 5-aminoimidazo[1,2-a]pyridine derivatives has been extended by a novel acid-induced dealkyation reaction that removes the 1,1,3,3-tetramethylbutyl group derived from the isonitrile input. This reaction was conducted on the solid-phase using the HMBA linker and the resulting products subjected to reductive alkylation using several aldehydes, thereby accessing novel substitution patterns at the 3-position. (C) 2000 Elsevier Science Ltd.. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00003-4
• 作为产物：
  描述：

  对醛基苯甲酸 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 4-(3-Amino-imidazo[1,2-a]pyrazin-2-yl)-benzoic acid methyl ester
  参考文献：
  名称：

  A novel dealkylation affording 3-aminoimidazo[1,2-a]pyridines: access to new substitution patterns by solid-phase synthesis

  摘要：

  The three-component synthesis of 5-aminoimidazo[1,2-a]pyridine derivatives has been extended by a novel acid-induced dealkyation reaction that removes the 1,1,3,3-tetramethylbutyl group derived from the isonitrile input. This reaction was conducted on the solid-phase using the HMBA linker and the resulting products subjected to reductive alkylation using several aldehydes, thereby accessing novel substitution patterns at the 3-position. (C) 2000 Elsevier Science Ltd.. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00003-4